| Revision as of 14:06, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 463684752 of page Trifluoromethanesulfonyl_azide for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 22:03, 12 March 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,203 edits ref |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 413808660 |
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| verifiedrevid = 470614537 |
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| ImageFile = Trifluoromethanesulfonyl azide.png |
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| ImageFile = Trifluoromethanesulfonyl azide.png |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| ImageFileR1 = Trifluoromethanesulfonyl azide Space Fill.png |
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| IUPACName = ''N''-diazo-1,1,1-trifluoro-methanesulfonamide |
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| ImageSizeR1 = 150px |
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| ImageFileL1 = Trifluoromethanesulfonyl azide Ball and Stick.png |
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| ImageSizeL1 = 175px |
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| PIN = Trifluoromethanesulfonyl azide |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| InChI = 1/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5 |
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| InChI = 1/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5 |
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| InChIKey = NQPHMXWPDCSHTE-UHFFFAOYAT |
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| InChIKey = NQPHMXWPDCSHTE-UHFFFAOYAT |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI =1S/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5 |
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| StdInChI = 1S/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NQPHMXWPDCSHTE-UHFFFAOYSA-N |
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| StdInChIKey = NQPHMXWPDCSHTE-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 3855-45-6 --> |
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| PubChem = 10986786 |
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| CASNo = 3855-45-6 |
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| PubChem = 10986786 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 9161983 |
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| ChemSpiderID = 9161983 |
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| SMILES = FC(F)(F)S(=O)(=O)N== |
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| SMILES = FC(F)(F)S(=O)(=O)N== |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = {{chem2|CF3SO2N3}} |
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| C = 1 | F = 3 | N = 3 | O = 2 | S = 1 |
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| C=1|F=3|S=1|O=2|N=3 |
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| Appearance = |
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| Density = |
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| Appearance = |
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| MeltingPt = |
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| Density = |
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| BoilingPt = |
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| MeltingPt = 80-81 °C |
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| Solubility =insoluble<ref name = cavender/> |
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| BoilingPt = |
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| Solubility =insoluble<ref name = cavender/> |
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}} |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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}} |
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}} |
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}} |
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}} |
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'''Trifluoromethanesulfonyl azide''' or '''triflyl azide''' {{chem2|CF3SO2N3}} is an organic ] used as a reagent in ].<ref>{{cite book |doi=10.1002/047084289X.rn00114.pub2 |chapter=Trifluoromethanesulfonyl Azide |title=Encyclopedia of Reagents for Organic Synthesis |date=2009 |last1=Bernet |first1=Bruno |last2=Vasella |first2=Andrea |last3=Liu |first3=Qi |last4=Tor |first4=Yitzhak |isbn=978-0-471-93623-7 }}</ref> |
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==Preparation== |
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Trifluoromethanesulfonyl azide is prepared by treating ] with ], traditionally in ].<ref name = cavender>{{cite journal |author1=C. J. Cavender |author2=V. J. Shiner |name-list-style=amp | title = Trifluoromethanesulfonyl azide. Its reaction with alkyl amines to form alkyl azides | journal = ] | volume = 37 | issue = 22 | pages = 3567–3569 | doi = 10.1021/jo00795a052 | year = 1972}}</ref> However, the use of dichloromethane is avoided since it can generate highly explosive azido-chloromethane and diazidomethane. The reaction may also instead be conducted in ],<ref>Titz, A.; Radic, Z.; Schwardt, O.; Ernst, B. Tetrahedron Lett. (2006), 47, 2383.</ref> ], or ].<ref>{{cite journal | author = R.-B. Yan, F. Yang, Y. Wu, L.-H. Zhang and X.-S. Ye | title = An efficient and improved procedure for preparation of triflyl azide and application in catalytic diazotransfer reaction | journal = ] | volume = 46 | issue = 52 | pages = 8993–8995 | doi = 10.1016/j.tetlet.2005.10.103 | year = 2005}}</ref> |
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:{{chem2|Tf2O + NaN3 → TfN3 + NaOTf}} (Tf = {{chem2|CF3SO2}}) |
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An alternative route starts from ].<ref>{{cite journal |author1=E. D. Goddard-Borger |author2=R. V. Stick |name-list-style=amp | title = An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride | journal = ] | volume = 9 | issue = 19 | pages = 3797–3800 | doi = 10.1021/ol701581g | pmid = 17713918 | year = 2007}}</ref> |
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==Reactions== |
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Trifluoromethanesulfonyl azide generally converts amines to azides. |
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==See also== |
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* ] |
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* ] |
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* ] |
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==References== |
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<references/> |
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] |
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] |
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] |